Oxygen atom transfer from a chiral N-alkyl oxaziridine promoted by acid.: The asymmetric oxidation of sulfides to sulfoxides.

被引:50
作者
Bohé, L [1 ]
Lusinchi, M [1 ]
Lusinchi, X [1 ]
机构
[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France
关键词
D O I
10.1016/S0040-4020(98)01035-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral N-alkyl oxaziridines may be used as reagents for the asymmetric oxidation of sulfides in an acid-promoted reaction leading exclusively to the corresponding sulfoxides A planar transition state geometry seems consistent with the observed stereochemistry which should result from the steric interactions in the transition state. The influence of the solvent and the acid strength on the oxygen transfer reaction are discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:155 / 166
页数:12
相关论文
共 29 条
  • [1] ANDREAE S, 1991, SYNTHESIS-STUTTGART, P327
  • [2] [Anonymous], J AM CHEM SOC
  • [3] THE MECHANISM OF OXYGEN-TRANSFER FROM AN OXAZIRIDINE TO A SULFIDE AND A SULFOXIDE - A THEORETICAL-STUDY
    BACH, RD
    CODDENS, BA
    MCDOUALL, JJW
    SCHLEGEL, HB
    DAVIS, FA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (10) : 3325 - 3330
  • [4] CONFORMATIONAL STUDY OF SUBSTITUTED METHYL PHENYL SULFOXIDES - A MULTINUCLEAR (H-1, C-13, AND O-17) APPROACH
    BENASSI, R
    FOLLI, U
    IAROSSI, D
    MUCCI, A
    SCHENETTI, L
    TADDEI, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1989, (05): : 517 - 521
  • [5] BENASSI R, 1989, J MOL STRUC-THEOCHEM, V184, P261
  • [6] Oxygen atom transfer from a chiral oxaziridinium salt.: Asymmetric epoxidation of unfunctionalized olefins.
    Bohé, L
    Lusinchi, M
    Lusinchi, X
    [J]. TETRAHEDRON, 1999, 55 (01) : 141 - 154
  • [7] IMINES AND DERIVATIVES .20. N-PHOSPHINOYLOXAZIRIDINES - SYNTHESIS AND STRUCTURAL CHARACTERIZATION BY NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY AND A CRYSTAL-STRUCTURE OF 3-(4-CHLOROPHENYL)-2-(DIPHENYLPHOSPHINOYL)OXAZIRIDINE
    BOYD, DR
    MALONE, JF
    MCGUCKIN, MR
    JENNINGS, WB
    RUTHERFORD, M
    SAKET, BM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1988, (07): : 1145 - 1150
  • [8] C-13 NUCLEAR MAGNETIC-RESONANCE INVESTIGATION OF SOME SUBSTITUTED METHYL PHENYL SULFIDES, SULFOXIDES, AND SULFONES
    BUCHANAN, GW
    REYESZAM.C
    CLARKE, DE
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1974, 52 (23): : 3895 - 3904
  • [9] MECHANISMS OF PHOTOCHEMICAL REACTIONS IN SOLUTION .62. NAPHTHALENE SENSITIZED PHOTORACEMIZATION OF SULFOXIDES
    COOKE, RS
    HAMMOND, GS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (09) : 2739 - &
  • [10] CHEMISTRY OF OXAZIRIDINES .11. (CAMPHORYLSULFONYL)OXAZIRIDINE, SYNTHESIS AND PROPERTIES
    DAVIS, FA
    TOWSON, JC
    WEISMILLER, MC
    LAL, S
    CARROLL, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (25) : 8477 - 8482